Diethyl Ether → HCID 21515512, compound

HRID 1284024Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:15][CH3:16])[C:11]=1[CH:12]([CH3:14])C)[C:6](Cl)=[O:7].[NH:17]1[CH2:19][CH2:18]1.C([O:22]CC)C>>[C:12]([C:11]1[C:10]([O:15][CH3:16])=[CH:9][C:5]([C:6]2[O:7][CH2:19][CH2:18][N:17]=2)=[CH:4][C:3]=1[O:2][CH3:1])(=[O:22])[CH3:14]

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 9033Aziridine

HCID 2151549755703-62-3

Product 1

HCID 21515512HCID 21515512, compound

Procedure

3,5-Dimethoxy-4-isopropyl-benzoyl chloride. The compound prepared under G) is first reacted with aziridine according to the procedure described by D. Haidukewych et al., Tetrahedron Letters, 30, 3031-3034, 1972, obtaining 4-acetyl-3,5-dimethoxy-1-(2-oxazolinyl)-benzene, m.p. 135°-37°C (diethyl ether). This compound is reacted with magnesium methyl iodide and 2-[2,6-dimethoxy-4-(2-oxazolinyl)]phenyl-2-propanol is obtained (m.p. 113°-16°C, from diisopropylether), from which, by treatment with sulphuric acid 3,5-dimethoxy-4-isopropenyl-benzoic acid is prepared. M.p. 169°-73°C (from ethanol/water). Said compound is hydrogenated to 3,5-dimethoxy-4-isopropyl-benzoic acid(m.p. 180°-83°C, from diethylether/light petroleum): the corresponding chloride melts at 75°-78°C (from light petroleum upon cooling).

Workup

customThe compound prepared under G)

Sources & evidence

ORD record: ord-1e78cf523d1840c09c819ae4bc586e3e
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03978065

Reaction notes

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